59862-56-5Relevant academic research and scientific papers
One-pot synthesis of 2-amino-3,4-dicyanopyridines from ketoximes and tetracyanoethylene via Cu(I)-catalyzed cyclization
Han, Ziwei,Lv, Jianguang,Zhang, Jianmin
supporting information, p. 2162 - 2168 (2019/02/25)
A novel approach to 2-amino-3,4-dicyanopyridines has been discovered from Cu(I)-catalyzed cyclizations of simple and easily available ketoximes and tetracyanoethylene (TCNE). The complexed radical mechanism involves cleavage of several O[sbnd]H/N[sbnd]O/C
Copper-catalyzed synthesis of oxime ethers from iminoxy radical (C[dbnd]N–O[rad]) and maleimides via radical addition
Han, Ziwei,Shen, Subo,Zheng, Feng,Hu, Han,Zhang, Jianmin,Zhu, Shizheng
supporting information, (2019/09/30)
An efficient Cu(II)-catalyzed radical addition of maleimides has been achieved. The identified copper catalyst enables the formation of oxime radicals (N–O[rad]) by cleaving the O–H bond in ketoximes, followed by the radical addition to N-substituted male
Stereospecific synthesis of 1,5-disubstituted tetrazoles from ketoximes via a Beckmann rearrangement facilitated by diphenyl phosphorazidate
Ishihara, Kotaro,Shioiri, Takayuki,Matsugi, Masato
supporting information, p. 1295 - 1298 (2019/04/13)
A novel method for the stereospecific synthesis of 1,5-disubstituted tetrazoles from ketoximes via the Beckmann rearrangement was developed using diphenyl phosphorazidate (DPPA) as both the oxime activator and azide source. Various ketoximes were transformed into the corresponding 1,5-disubstituted tetrazoles with exclusive trans-group migration and no E-Z isomerization of the ketoxime. This method enables the preparation of 1,5-disubstituted tetrazoles without using toxic or explosive azidation reagents.
A mild system for synthesis of aldoximes and ketoximes in the presence of N-hydroxyphthalimide in aqueous system
Jiang, Xiaoying,Xu, Xiaohe,Lin, Yuyan,Yan, Yiyan,Li, Pingping,Bai, Renren,Xie, Yuanyuan
supporting information, p. 5879 - 5885 (2018/09/06)
An efficient method for synthesis of oximes from aldehydes or ketones with N-hydroxyphthalimide or N-hydroxysuccinimide in water has been described. It is the first time to utilize NHPI as an oximation reagent to synthesize aldoximes and ketoximes from the corresponding organic carbonyl compounds without other reagents. The reaction tolerates various functional groups and affords the corresponding oximes in 76%–98% yields. The by-product phthalic acid can be recycled from the system. In addition, this method has been successfully applied to the synthesis of the precursor of some pharmacologically active amide molecules.
Evaluation of Substituted 1,2,3-Dithiazoles as Inhibitors of the Feline Immunodeficiency Virus (FIV) Nucleocapsid Protein via a Proposed Zinc Ejection Mechanism
Asquith, Christopher R. M.,Konstantinova, Lidia S.,Laitinen, Tuomo,Meli, Marina L.,Poso, Antti,Rakitin, Oleg A.,Hofmann-Lehmann, Regina,Hilton, Stephen T.
, p. 2119 - 2126 (2016/10/22)
A diverse library of 5-thieno-, 5-oxo-, and 5-imino-1,2,3-dithiazole derivatives was synthesized and evaluated for efficacy against the feline immunodeficiency virus (FIV) as a model for HIV in cells. Several diverse compounds from this series displayed n
An efficient catalytic method for the Beckmann rearrangement of ketoximes to amides and aldoximes to nitriles mediated by propylphosphonic anhydride (T3P)
Augustine, John Kallikat,Kumar, Rajesha,Bombrun, Agnes,Mandal, Ashis Baran
experimental part, p. 1074 - 1077 (2011/03/22)
An efficient method for the Beckmann rearrangement of ketoximes to amides mediated by a catalytic amount (15 mol %) of propylphosphonic anhydride (T3P) is described. Aldoximes underwent second order Beckmann rearrangement to provide the corresponding nitriles in excellent yields on reacting with T3P (15 mol %) at room temperature. The main advantages of this environmentally friendly protocol include procedural simplicity, and particularly ease of isolation of the products.
Synthesis of highly substituted pyrroles via nucleophilic catalysis
Ngwerume, Simbarashe,Camp, Jason E.
supporting information; experimental part, p. 6271 - 6274 (2010/11/19)
Figure presented. A nucleophilic catalysis method providing a concise synthesis of di-, tri-, and tetrasubstituted pyrroles is described. This regioselective one-pot method relies on nucleophilic catalysis of the intermolecular addition of oximes to activ
Synthesis, larvicidal activity, and SAR studies of new benzoylphenylureas containing oxime ether and oxime ester group
Sun, Ranfeng,Li, Yongqiang,Lue, Maoyun,Xiong, Lixia,Wang, Qingmin
supporting information; experimental part, p. 4693 - 4699 (2010/10/02)
A series of new structural benzoylphenylureas (BPUs) containing oxime ether and oxime ester group were designed and synthesized. The larvicidal activities against Oriental armyworm and mosquito of these benzoylphenylureas were evaluated and the result of bioassay displayed specific structure-activity relationship (SAR). Most of the compounds exhibited excellent larvicidal activities against Oriental armyworm and mosquito. Interestingly, some compounds showed different structure-activity relationship towards diamondback moth, beet armyworm, and corn borer although three tested insects all belong to the same insect order.
Gas-phase acidities of acetophenone oximes. Substituent effect and solvent effects
Badal, Mizanur Rahman,Mishima, Masaaki
experimental part, p. 58 - 65 (2010/03/25)
Gas-phase acidities (GA) of ring-substituted (E)-acetophenone oximes, XC6H4C(CH3)=NOH, were determined by measuring proton-transfer equilibria using an FT-ICR mass spectrometer. The magnitude of the substituent effect on t
Asymmetric reduction of oxime ethers promoted by chiral spiroborate esters with an O3BN framework
Chu, Yunbo,Shan, Zixing,Liu, Dejun,Sun, Nannan
, p. 3998 - 4001 (2007/10/03)
Enatioselective reduction of oxime ethers promoted by chiral spiroborate esters with an O3BN framework is reported for the first time. In the presence of (R,S)-1, 11 aralkyloxime ethers are reduced by borane-THF at 0-5 °C to give (S)-1-aralkylamine in high yield and excellent enatiomeric excess (up to 98% ee). Influence of reaction conditions on the enantioselectivity of the reduction is investigated, and a possible mechanism of the catalytic reduction is suggested.
